((3-((2R,3aS,4S,6S,7aR)-3a-(benzyloxy)-2-methoxy-4-((4-methoxybenzyl)oxy)hexahydro-4H-furo[2,3-b]pyran-6-yl)prop-2-yn-1-yl)oxy)(tert-butyl)diphenylsilane

Base Information

Chemical Name:((3-((2R,3aS,4S,6S,7aR)-3a-(benzyloxy)-2-methoxy-4-((4-methoxybenzyl)oxy)hexahydro-4H-furo[2,3-b]pyran-6-yl)prop-2-yn-1-yl)oxy)(tert-butyl)diphenylsilane
CAS No.:1141494-29-2
Molecular Formula:C₄₂H₄₈O₇Si
Molecular Weight:692.924
Hs Code.:

Synonyms:((3-((2R,3aS,4S,6S,7aR)-3a-(benzyloxy)-2-methoxy-4-((4-methoxybenzyl)oxy)hexahydro-4H-furo[2,3-b]pyran-6-yl)prop-2-yn-1-yl)oxy)(tert-butyl)diphenylsilane

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Chemical Property of ((3-((2R,3aS,4S,6S,7aR)-3a-(benzyloxy)-2-methoxy-4-((4-methoxybenzyl)oxy)hexahydro-4H-furo[2,3-b]pyran-6-yl)prop-2-yn-1-yl)oxy)(tert-butyl)diphenylsilane

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Technology Process of ((3-((2R,3aS,4S,6S,7aR)-3a-(benzyloxy)-2-methoxy-4-((4-methoxybenzyl)oxy)hexahydro-4H-furo[2,3-b]pyran-6-yl)prop-2-yn-1-yl)oxy)(tert-butyl)diphenylsilane

There total 14 articles about ((3-((2R,3aS,4S,6S,7aR)-3a-(benzyloxy)-2-methoxy-4-((4-methoxybenzyl)oxy)hexahydro-4H-furo[2,3-b]pyran-6-yl)prop-2-yn-1-yl)oxy)(tert-butyl)diphenylsilane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 52.0%

: 1141494-19-0
(3aS,4S,6S,7aR)-3a-benzyloxy-6-(3-tert-butyldiphenylsilyloxyprop-1-ynyl)-4-hydroxy-2-methoxyhexahydro-2H-furo[2,3-b]pyran

: 2746-25-0
p-Methoxybenzyl bromide

: 1141494-20-3
(3aS,4S,6S,7aR)-3a-benzyloxy-6-(3-tert-butyldiphenylsilyloxyprop-1-ynyl)-2(S)-methoxy-4-para-methoxybenzyloxyhexahydro-2H-furo[2,3-b]pyran

: 1141494-29-2
((3-((2R,3aS,4S,6S,7aR)-3a-(benzyloxy)-2-methoxy-4-((4-methoxybenzyl)oxy)hexahydro-4H-furo[2,3-b]pyran-6-yl)prop-2-yn-1-yl)oxy)(tert-butyl)diphenylsilane

Guidance literature:: (3aS,4S,6S,7aR)-3a-benzyloxy-6-(3-tert-butyldiphenylsilyloxyprop-1-ynyl)-4-hydroxy-2-methoxyhexahydro-2H-furo[2,3-b]pyran; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.0833333h;

p-Methoxybenzyl bromide; With tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 2h;
DOI:10.1002/anie.200805395

Reference yield:

: tert-butyl((3-((2S,3aS,5S,6aR,8R,9aS)-8-methoxy-2-(4-methoxyphenyl)tetrahydro-5H,6aH-[1,3]dioxolo[4,5-c]furo[2,3-b]pyran-5-yl)prop-2-yn-1-yl)oxy)diphenylsilane

: 100-39-0
benzyl bromide

: 1141494-29-2
((3-((2R,3aS,4S,6S,7aR)-3a-(benzyloxy)-2-methoxy-4-((4-methoxybenzyl)oxy)hexahydro-4H-furo[2,3-b]pyran-6-yl)prop-2-yn-1-yl)oxy)(tert-butyl)diphenylsilane

Guidance literature:: tert-butyl((3-((2S,3aS,5S,6aR,8R,9aS)-8-methoxy-2-(4-methoxyphenyl)tetrahydro-5H,6aH-[1,3]dioxolo[4,5-c]furo[2,3-b]pyran-5-yl)prop-2-yn-1-yl)oxy)diphenylsilane; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.5h; Inert atmosphere;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 2h; Inert atmosphere;
DOI:10.1021/acs.orglett.5b00831

Reference yield:

: C₂₁H₃₆O₇Si

: 1141494-29-2
((3-((2R,3aS,4S,6S,7aR)-3a-(benzyloxy)-2-methoxy-4-((4-methoxybenzyl)oxy)hexahydro-4H-furo[2,3-b]pyran-6-yl)prop-2-yn-1-yl)oxy)(tert-butyl)diphenylsilane

Guidance literature:: Multi-step reaction with 11 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: chloro-trimethyl-silane; sodium iodide / acetonitrile / 0.33 h / -20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 1.5 h / -78 °C / Inert atmosphere

4.1: triethylamine / dichloromethane / 2 h / -15 °C / Inert atmosphere

5.1: ozone / dichloromethane / -78 °C

5.2: 4 h / -78 - 20 °C

6.1: silver(l) oxide / acetonitrile / 36 h / 20 °C / Inert atmosphere

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

8.1: camphor-10-sulfonic acid / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

9.1: potassium carbonate / methanol / 1 h / 0 °C / Inert atmosphere

10.1: 1H-imidazole / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

11.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

11.2: 2 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; chloro-trimethyl-silane; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; silver(l) oxide; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile; mineral oil;
DOI:10.1021/acs.orglett.5b00831